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Answer all the questions.

1 Bromine is a reactive element. It combines with other non-metals to form covalent compounds.
Phosphorus tribromide, PBr3, and iodine monobromide, IBr, are examples of covalent compounds used in
organic synthesis.

(a) PBr3 can be prepared by heating bromine with phosphorus, P4.

(i) Write an equation for this reaction.

…………………………………………………………………………………………. [1]

(ii) How many molecules are present in 1.3535 g of PBr3?

number of molecules = ……………………… [3]

(iii) The ‘dot-and-cross’ diagram of a molecule of PBr3 is given below.

Name the shape of this molecule and explain why the molecule has this shape.

name: ………………………………………………………………………………………..

explanation: ………………………………………………………………………………….

……………………………………………………………………………………………….

……………………………………………………………………………………………….

[3]

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(b) Bromine reacts with iodine to form iodine monobromide, IBr.

The table below lists some average bond enthalpies which are required in different parts of this
question.

Bond Average bond enthalpy / kJ mol1

Br–Br +193
I–I +151
I–Br +175

(i) Average bond enthalpy is the enthalpy change for the breaking of 1 mole of bonds in
gaseous molecules.

Why do Br2 and I2 not exist in the gaseous state under standard conditions?

……………………………………………………………………………………………….

……………………………………………………………………………………….. [1]

(ii) Calculate the enthalpy change of formation, fH, for IBr.

fH = ……………………… kJ mol1 [2]

(c) Iodine monobromide, I–Br, is a polar molecule.

Heterolytic fission of the I–Br bond forms an electrophile.

State the meaning of the term electrophile and suggest the formula of the electrophile formed from
IBr.

……………………………………………………………………………………………….

……………………………………………………………………………………….. [2]

(d) Bromine disproportionates when it reacts with potassium hydroxide solution.

Suggest an equation for this reaction.

……………………………………………………………………………………………… [1]

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2 A large proportion of the world’s output of organic chemicals is used to make addition polymers. These
polymers have a variety of uses.

(a) Poly(propene) is used to make packaging, textiles and rope.

A repeat unit for poly(propene) is shown below.

(i) Explain why poly(propene) is a saturated hydrocarbon.

……………………………………………………………………………………………….

………………………………………………………………………………………….. [1]

(ii) State the bond angle around each carbon atom in poly(propene).

………………………………………………………………………………………….. [1]

(iii) After polymers have been used for packaging, the waste polymers need to be processed to save
resources, for example, by recycling.

Describe two other ways in which waste poly(propene) can be processed in a sustainable way.

……………………………………………………………………………………………….

……………………………………………………………………………………………….

……………………………………………………………………………………………….

…………………………………………………………………………………………. [2]

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3 Compound A is an alkene.

H 3C CH3

C C

H CH3
compound A

(a) The C=C bond in a molecule of compound A has restricted rotation because it comprises a
σ bond and a π bond.

(i) Describe one difference between the σ bond and the π bond.

...........................................................................................................................................

...........................................................................................................................................

...........................................................................................................................................

...................................................................................................................................... [1]

(ii) Explain why compound A does not have E/Z isomers.

...........................................................................................................................................

...........................................................................................................................................

...................................................................................................................................... [1]

(iii) A structural isomer of compound A has E/Z isomers.

Draw the structure of the Z isomer and then name this isomer.

structure of Z isomer

name ........................................................................
[2]

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(b) Compound A can be made from alcohol B by heating with an acid catalyst.

Suggest two possible structures for alcohol B.

[2]

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6 Two reactions of compound C are shown in the flowchart below.

H Cl

C C

H Cl
Compound C

Reaction 1 Reaction 2

H Cl H Cl

H C C OH H C C Cl

H Cl Br Br
Compound D

(a) State the reagents and conditions for reaction 1.

...................................................................................................................................................

.............................................................................................................................................. [1]

(b) In reaction 2, compound C reacts with bromine to form compound D.

(i) Give the systematic name of compound D.

...................................................................................................................................... [1]

(ii) Outline the mechanism for reaction 2.

Include curly arrows, charges and relevant dipoles.

[3]

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(c) Compound C forms an addition polymer E.

(i) Write a balanced equation for this reaction.

Show displayed formulae.

[2]

(ii) State one advantage and one disadvantage of using combustion as a method for the
disposal of waste polymer E.

Advantage .........................................................................................................................

...........................................................................................................................................

Disadvantage ....................................................................................................................

...................................................................................................................................... [2]

© OCR 2018 Turn over

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26 Compound B, shown below, can be used to synthesise organic compounds with different functional
groups.

H CH3

C C

H CH3
Compound B

(a) (i) Compound B is a member of a homologous series.

Name the homologous series and state its general formula.

Homologous series ...........................................................................................................

General formula ............................................................................................................ [1]

(ii) What reagents and conditions are needed to convert compound B into a saturated
hydrocarbon?

...................................................................................................................................... [1]

(b) Some reactions involving compound B are shown in the flowchart below.

Complete the flowchart, showing the structures of organic compounds C and D.

H CH3
concentrated
C C
H2SO4, heat
H CH3
Compound C Compound B

K2Cr2O7 / H2SO4 polymerisation

reflux

no reaction

Compound D (repeat unit)

[2]

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(c) The structure of compound F is shown below.

H CH3

HO C C OH

H CH3
Compound F

(i) What is the empirical formula of compound F?

...................................................................................................................................... [1]

(ii) A student plans a two-stage synthesis for preparing compound F from compound B.

The synthesis first prepares compound E, as shown in the flowchart.

Draw the structure of compound E in the box and state the reagents for each stage on
the dotted lines.

H CH3
.........................
C C
stage 1
H CH3
Compound B Compound E

stage 2 .........................

H CH3

HO C C OH

H CH3
Compound F
[3]

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6 This question is about the properties and reactions of butan-2-ol.

H H H H

H C C C C H

H OH H H

Some properties of butan-2-ol are listed in the table.

Melting point –115 °C

Boiling point 99.5 °C

(a) Why is butan-2-ol classified as a secondary alcohol?

...................................................................................................................................................

.............................................................................................................................................. [1]

(b) The shape around the oxygen atom in butan-2-ol is non-linear.

Predict the C–O–H bond angle and explain this shape.

bond angle ......................................................

explanation ...............................................................................................................................

...................................................................................................................................................

...................................................................................................................................................

...................................................................................................................................................

.............................................................................................................................................. [4]

(c) Butan-2-ol can be oxidised by heating with an oxidising agent.

(i) Write an equation for the reaction.

Use [O] to represent the oxidising agent and show the structure of the organic product.

[2]

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(ii) A student plans to carry out this oxidation using the apparatus shown in the diagram.

Give one reason why the apparatus is not suitable and describe a more suitable way of
carrying out this oxidation.

...........................................................................................................................................

...........................................................................................................................................

...................................................................................................................................... [2]

(d) 20.2 g of butan-2-ol is reacted with excess sodium bromide and sulfuric acid.

CH3CH(OH)CH2CH3 + NaBr + H2SO4 CH3CHBrCH2CH3 + NaHSO4 + H2O

25.2 g of CH3CHBrCH2CH3 is formed.

Calculate the percentage yield of CH3CHBrCH2CH3.

percentage yield = ..................................................... % [3]

Dr.Malik Imran Afzal Ph.D Chemistry